Nitrogen → tert-Butyl 3,3-difluoro-4-oxopiperidine-1-carboxylate

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of tert-butyl 3,3-difluoro-4-hydroxypiperidine-1-carboxylate (2.40 g, 10.00 mmol) in dry CH2Cl2 (50 mL) was added a solution of Dess-Martin periodinane (50 mL of a 15% solution in CH2Cl2, 24.00 mmol). The reaction mixture was stirred at rt until completion of the reaction. Sat. aq. NaHCO3 (50 mL) was then added followed by 10% aq. Na2SO3 (50 mL). The mixture was stirred at rt for 1 h, the layers separated and the aq. layer extracted with CH2Cl2 (3×). The combined org. extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was redissolved in CH2Cl2 (30 mL) and stirred in the presence of molecular sieves for 24 h, filtered, and concentrated under reduced pressure to give tert-butyl 3,3-difluoro-4-oxopiperidine-1-carboxylate as a yellow solid.

Provenance & Evidence